2-{2-[(9-butoxy-5',5'-dimethyl-6,7-dihydrospiro[dibenzo[a,e]cyclopropa[c][8]annulene-1,2'-[1,3]dioxan]-4-yl)oxy]ethoxy}ethyl 4-nitrophenyl carbonate | 1239744-72-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-{2-[(9-butoxy-5',5'-dimethyl-6,7-dihydrospiro[dibenzo[a,e]cyclopropa[c][8]annulene-1,2'-[1,3]dioxan]-4-yl)oxy]ethoxy}ethyl 4-nitrophenyl carbonate
• 英文别名: 2-{2-[(9-butoxy-5',5'-dimethyl-6,7-dihydrospiro[dibenzo[a,e]cyclopropa[c][8]annulen-1,2'-[1',3']dioxan]-4-yl)oxy]ethoxy}ethyl-4-nitrophenylcarbonate；2-{2-[(9-Butoxy-5',5'-dimethyl-6,7-dihydrospiro-[dibenzo[a,e]cyclopropa[c][8]annulene-1,2'-[1,3]dioxan]-4-yl)oxy]ethoxy}ethyl 4-nitrophenyl carbonate；2-[2-(15'-butoxy-5,5-dimethylspiro[1,3-dioxane-2,3'-tetracyclo[11.4.0.02,4.05,10]heptadeca-1(13),2(4),5(10),6,8,14,16-heptaene]-8'-yl)oxyethoxy]ethyl (4-nitrophenyl) carbonate
• CAS: 1239744-72-9
• 化学式: C₃₇H₄₁NO₁₀
• 分子量: 659.733
• InChiKey: YLQKPIVDNUMSNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  48
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-{2-[(9-butoxy-5',5'-dimethyl-6,7-dihydrospiro[dibenzo[a,e]cyclopropa[c][8]annulene-1,2'-[1,3]dioxan]-4-yl)oxy]ethoxy}ethyl 4-nitrophenyl carbonate 、 N-生物素-3,6-二氧杂辛烷-1,8-二胺 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 2-(2-((4-butoxy-5',5'-dimethyl-6,7-dihydrospiro[dibenzo[a,e]cyclopropa[c][8]annulene-1,2'-[1,3]dioxan]-9-yl)oxy)ethoxy)ethyl (2-(2-(2-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)ethoxy)ethoxy)ethyl)carbamate
  参考文献：
  名称：

  Selective Labeling of Living Cells by a Photo-Triggered Click Reaction

  摘要：

  Phototriggering of the metal-free azide to acetylene cycloaddition reaction was achieved by masking the triple bond of dibenzocyclooctynes as cyclopropenone. Such masked cyclooctynes do not react with azides in the dark. Irradiation of cyclopropenones results in the efficient (Phi(355) = 0.33) and clean regeneration of the corresponding dibenzocyclooctynes, which then undergo facile catalyst-free cycloadditions with azides to give corresponding triazoles under ambient conditions. In situ light activation of a cyclopropenone linked to biotin made it possible to label living cells expressing glycoproteins containing N-azidoacetyl-sialic acid. The cyclopropenone-based phototriggered click chemistry offers exciting opportunities to label living organisms in a temporally and spatially controlled manner and may facilitate the preparation of microarrays.

  DOI：

  10.1021/ja9054096
• 作为产物：
  描述：

  2-{2-[(9-butoxy-5',5'-dimethyl-6,7-dihydrospiro[dibenzo[a,e]cyclopropa[c][8]annulene-1,2'-[1,3]dioxan]-4-yl)oxy]ethoxy}ethanol 、 对硝基苯基氯甲酸酯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以80%的产率得到2-{2-[(9-butoxy-5',5'-dimethyl-6,7-dihydrospiro[dibenzo[a,e]cyclopropa[c][8]annulene-1,2'-[1,3]dioxan]-4-yl)oxy]ethoxy}ethyl 4-nitrophenyl carbonate
  参考文献：
  名称：

  Cyclopropenones and the Photochemical Generation of Cyclic Alkynes Therefrom

  摘要：

  环状炔烃（例如，二苯并环辛烯等）可以从环丙酮烯光化学地生成，如本文所披露的。这些环状炔烃可以与具有炔烃反应基团（例如，“点击”反应中的偶氮基团）的材料发生反应（例如，在原位）。在优选实施例中，环状炔烃的生成和反应可以在无催化剂（例如，Cu(I)）的情况下进行。这些反应可以用于例如，用于选择性标记通过含有偶氮基团表面单糖代谢修饰的活细胞，或用于光导向表面图案。

  公开号：

  US20100210854A1

文献信息

• Cyclopropenones and the Photochemical Generation of Cyclic Alkynes Therefrom
  申请人：Popik Vladimir V.

  公开号：US20100210854A1

  公开（公告）日：2010-08-19

  Cyclic alkynes (e.g., cyclooctynes such as dibenzocyclooctynes) can be photochemically generated from cyclopropenones as disclosed herein. The cyclic alkynes can be reacted (e.g., in situ) with materials having alkyne-reactive groups (e.g., azide groups in a “click” reaction). In preferred embodiments, the generation and reaction of the cyclic alkyne can proceed in the absence of a catalyst (e.g., Cu(I)). These reactions can be useful, for example, for the selective labeling of living cells that are metabolically modified with azido-containing surface monosaccharides, or for light-directed surface patterning.

  环状炔烃（例如，二苯并环辛烯等）可以从环丙酮烯光化学地生成，如本文所披露的。这些环状炔烃可以与具有炔烃反应基团（例如，“点击”反应中的偶氮基团）的材料发生反应（例如，在原位）。在优选实施例中，环状炔烃的生成和反应可以在无催化剂（例如，Cu(I)）的情况下进行。这些反应可以用于例如，用于选择性标记通过含有偶氮基团表面单糖代谢修饰的活细胞，或用于光导向表面图案。
• Cyclopropenones and the photochemical generation of cyclic alkynes therefrom
  申请人：University of Georgia Research Foundation, Inc.

  公开号：US08258347B2

  公开（公告）日：2012-09-04

  Cyclic alkynes (e.g., cyclooctynes such as dibenzocyclooctynes) can be photochemically generated from cyclopropenones as disclosed herein. The cyclic alkynes can be reacted (e.g., in situ) with materials having alkyne-reactive groups (e.g., azide groups in a “click” reaction). In preferred embodiments, the generation and reaction of the cyclic alkyne can proceed in the absence of a catalyst (e.g., Cu(I)). These reactions can be useful, for example, for the selective labeling of living cells that are metabolically modified with azido-containing surface monosaccharides, or for light-directed surface patterning.

  本文披露了从环丙酮类化合物中光化学生成环炔（例如二苯并环辛炔）的方法。环炔可以与具有炔基反应性基团的材料（例如“点击”反应中的偶氮基团）反应（例如原位反应）。在优选实施例中，生成和反应环炔可以在无催化剂（例如Cu（I））的情况下进行。这些反应可以用于例如选择性标记代谢修饰有偶氮基团表面单糖的活细胞，或进行光驱动表面图案化等方面。
• US8258347B2
  申请人：——

  公开号：US8258347B2

  公开（公告）日：2012-09-04
• US8426649B2
  申请人：——

  公开号：US8426649B2

  公开（公告）日：2013-04-23
• US8541625B2
  申请人：——

  公开号：US8541625B2

  公开（公告）日：2013-09-24